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08.27.124:45 AM ET

New Clues in the Mysterious Disappearance of Multimillionaire Guma Aguiar

Energy tycoon and prominent Zionist Guma Aguiar disappeared off the Florida coast in June. Whether he died in an accident, killed himself, or staged his own death remains one of the year’s most intriguing mysteries. Now his close friends are telling their side.

With cloudy skies overhead, Brazilian-American multimillionaire Guma Aguiar stepped onto his 31-foot fishing boat Zion in Ft. Lauderdale, Fla., on June 19 and set sail. The next day the Zion drifted ashore, its light and engine still on, but its owner missing. In the two months that followed, the unexplained disappearance of the 35-year-old energy tycoon sparked a ferocious battle in Florida courts, with Aguiar’s wife and mother moving separately to gain control of his estimated $100 million fortune.

What happened out there on the high seas remains a mystery. If Aguiar died, was it accidental or deliberate? Or was it, in fact, an elaborate ruse, as some have speculated? Did he fake his own death to escape mounting legal trouble and financial losses?

Interviews with a half dozen of his close friends and advisers, including several who had never spoken publicly about the case, offer new clues into Aguiar’s state of mind leading up to that fateful day and undermine the theory that he’s hiding out in some remote locale. Their stories paint a picture of a bullish, athletic self-starter, someone who wasn’t one to run from trouble and who had big plans to use his wealth to change the world. But they also show someone who was chased by a terrible darkness, prone to fits of depression and extreme, unpredictable behavior that may have figured in an untimely death.

“If he had just been left alone, he would have been able to complete some of his plans,” said Harvard professor Alan Dershowitz, Aguiar’s friend and legal adviser. Dershowitz says the tycoon, who had recently begun exploring his Jewish roots, wanted to use his influence as an investor in two big Israeli sports franchises to promote peace in the Middle East. At the time of his disappearance, he was also working on plans to build a giant center of Hasidic Judaism in the heart of Jerusalem.

The detective heading up the missing-person case in Florida declined to comment to The Daily Beast, but a spokesman for the Ft. Lauderdale Police Department said that while the investigation into Aguiar’s whereabouts remains open, there have been no significant leads in the case. With Aguiar’s wealth and connections, “it would be quite easy for him to stage his own disappearance, and it would be very difficult for us to find him,” Ft. Lauderdale police detective Travis Mandell said last month.

“Sometimes he would go into overdrive, almost like it was a fantasy but it was real to him.”

Aguiar made his fortune with the help of his uncle Thomas Kaplan, a billionaire philanthropist and president of the board of directors of Manhattan’s 92nd Street Y. The two would ultimately become bitter adversaries locked in legal battles over the proceeds and future of the business they built together. In 2003 Aguiar and Kaplan formed Leor Energy, investing in a Texas natural-gas find that turned out to be immensely profitable. Kaplan had already made a fortune in South American silver mines, while Aguiar, only 26 at the time, had little real-world experience. He had spent one year as a business major at Clemson University, which he attended on a tennis scholarship, before dropping out.

Aguiar was tipped off to the gas find, known as the Deep Bossier fields, by geologist John Amoruso, whom he met in Houston through a mutual acquaintance. Amoruso says Aguiar’s inexperience wasn’t an issue: “He was a quick study, he was smart, and what we told him he absorbed.”

In 2006 Kaplan and Aguiar sold their stake in the gas fields to Canada’s Encana Oil and Gas for $2.55 billion, according to court documents filed later. The following year Aguiar, who had stayed on as CEO of Leor, was named executive of the year by Oil and Gas Investor. In a profile published by the trade magazine, he described the intimate relationship he had enjoyed with his uncle as the two worked to build their company. “Even though Tom rarely came to Houston and wasn’t involved in the day-to-day operations, he was always in the background guiding me in building the company,” Aguiar said. “We talked every day—he was my mentor—but he gave me more autonomy as time went on.”

In the years that followed the sale of Leor’s holdings, however, the relationship between Aguiar and his uncle appears to have soured. In 2008 Aguiar was fired from the company, according to court documents. By April 2012 there were two pending lawsuits. In one, Aguiar claimed he was entitled to half the money from the sale of the Bossier fields and sued Kaplan in Texas’s western district court on Dec. 30, 2008, for unspecified claims. Kaplan countersued, alleging that Aguiar had engaged in improper conduct while serving as an executive at the company. In the course of the suits, the two sides had lodged bitter personal attacks against one another.

By the time Aguiar went missing, he was spending “98 percent of his waking moments thinking about these kinds of problems,” says Ron Lowy, a Florida attorney whom Aguiar hired as his general counsel earlier this year.

Dershowitz also said the legal tussling took its toll on Aguiar. “His uncle is a ruthless man who would do anything to preserve a few dollars,” Dershowitz said.

In an emailed statement to The Daily Beast, Kaplan’s attorney, Harley Tropin, said, "Mr. Kaplan and his family continue to be saddened by news of Mr. Aguiar's disappearance and express deepest sympathies to the family. Mr. Kaplan and his family sincerely hope Mr. Aguiar is alive and well.” Tropin also echoed what has been alleged in Kaplan’s suit—that Aguiar had been engaged in “multiple acts of illegal behavior against Mr. Kaplan's family and other parties, including making personal and violent threats, tampering with witness material and terrorizing witnesses, and the hacking of email accounts.”

Yet this isn’t the Aguiar his friends say they knew and admired. Tovia Singer met Aguiar in 2003, the same year Leor Energy was founded. Singer, a rabbi in Monsey, N.Y., who works to return converts to Christianity back to Judaism and is the author of Let’s Get Biblical, says he helped Aguiar explore his Jewish roots. Though his mother was born a Jew, she had raised her son in the Christian faith. In 2007 Aguiar moved to Jerusalem with his new wife and high-school sweetheart, Jamie. He immersed himself in the city, buying an apartment building within a stone’s throw of the Western Wall.

“Whatever he did, the afterburners went on and he went full blast,” Singer said in an interview.

In 2008, for example, Aguiar created the Defender of Jerusalem award to recognize contributions made by public figures to the holy city and the Israeli state. The first year, the award went to Israeli President Shimon Peres, the next, to Texas Governor Rick Perry. A photo from the event, posted on the governor’s official website, shows a tan and scruffy Aguiar standing beside a clean-shaven Perry. They are holding up a picture of the Western Wall and the Dome of the Rock. That same year, Arkansas Governor Mike Huckabee interviewed Aguiar on his Fox News show, calling him “a young Israeli version, a combination of T. Boone Pickens and [Dallas Cowboys owner] Jerry Jones.”

Huckabee didn’t respond to requests for comment. A spokesperson for Perry said that she was “not aware of them having met any other time” aside from the award ceremony.

Aguiar’s deepening investment in Jewish spirituality was matched by his increased giving to religious causes. Among his most significant gifts was $8 million he gave to Nefesh B’Nefesh, a group that encourages Jews from North America and the United Kingdom to move to Israel.

He also poured his money into the cultural life of Jerusalem, investing $4 million into the city’s Beitar soccer team in 2009 instead of “some paintings or a nice house in New York,” as he told a reporter at the time. The next month he bought a $1.5 million stake in Hapoel Jerusalem, a professional basketball squad.

Aguiar’s decision to become involved in Israeli sports was tied in with a desire to take on a political role in Jewish life, says his friend Jerry Levine, a filmmaker who was working on a documentary with Aguiar about his life. Those ambitions, say Levine, were still only half baked when Aguiar disappeared.

“The idea was to use the ownership of a sports team” to catch the public’s attention, Levine said. He wanted to give thousands of dollars’ worth of soccer gear to kids in Gaza, for example. “Once you’re the owner of a team, people listen to you, and once you’ve got that platform, you’re a public figure. His vision was to become an ambassador of goodwill using sports.”

During happier times, Aguiar flourished in Jerusalem, said Singer, who often visited him there. The two would discuss holy Scripture, politics, and sports. Aguiar would take his family and Singer to dinner at Jerusalem’s luxurious King David Hotel. “We’ve all sat at dinner tables together, passing the chicken and laughing,” Singer said.

Starting in 2009, Aguiar also began fostering close ties to Chabad-Lubavitch, one of the largest sects of Hasidic Judaism, at the group’s centers in Brooklyn, Ft. Lauderdale, and Jerusalem. He donated generously to local Chabad centers. In 2009 alone, Aguiar gave half a million dollars toward Chabad-sponsored Passover seders around the world and another $770,000 to finance Chanukah celebrations. He also paid for 200 members of the Florida Chabad community to fly to Queens, N.Y., for a religious gathering. But his biggest project by far was a plan to build an extensive new headquarters for the sect in Jerusalem at Aguiar’s property. In a promotional video, the ruddy Aguiar discusses plans for the Chabad cultural center, which was to be called 770 Western Parkway—a homage to Chabad-Lubavitch’s world headquarters at 770 Eastern Parkway in Crown Heights, Brooklyn.

Sholom Lipskar, a Hasidic rabbi from Bal Harbour, Fla., said that in the heady afterglow of his success with Leor, Aguiar went to religion for a sense of stability. When Aguiar came to see him, they would rarely discuss his family, business interests, or legal struggles. Aguiar was more interested in talking about Menachem Mendel Schneerson, the spiritual founder of Chabad-Lubavitch. It was hard not to be moved by Aguiar’s enthusiasm for Judaism, Lipskar said.

“Sometimes he would go into overdrive,” Lipskar said. “Almost like it was a fantasy, but it was real to him. Like 770 Western Parkway.”

But while friends admired Aguiar’s passionate intensity, crediting it with driving both his philanthropic giving and his business success, court records suggest it might also have taken a darker turn on occasion. An order out of the U.S. District Court for the Southern District of Florida, where Kaplan and Leor filed a lawsuit against Aguiar in 2009, found that Aguiar suffered from bipolar disorder, alternating between manic highs and deep depressive lows. His history of mental illness stretches back to 1997, according to the findings of fact, when at age 19 he was compelled under the Baker Act, a Florida law that allows for involuntary commitment for mental health, to spend 12 days under psychiatric care.

According to the court's findings, Aguiar was involuntarily committed again in 2010, this time in Tel Aviv, Israel, at Abarbanel Medical Health Center, after his wife complained that he was “using drugs, drinking alcohol, talk[ing] a lot, not sleeping at night or during the day.”

The findings detail allegedly paranoid fantasies maintained by Aguiar, saying he “believes that he has been poisoned, that he was shot in the back from a helicopter, that snipers have been following him and that the medical staff at an Israeli hospital were injecting him with poison in order to kill him." Aguiar also “expressed the grandiose belief that he is or could be the Messiah.”

"Following these and other malicious and illegal activities, the Kaplan parties were granted orders of protection against Mr. Aguiar in Florida and New York courts," Tropin said in his statement to The Daily Beast. "Subsequently, after violation of the Florida court's order, the Federal District court in Miami threw out Mr. Aguiar's lawsuit against the Kaplan interests."

Indeed, Aguiar's claims against Kaplan and his interests, as well as his defensive pleadings in Kaplan's case against him, were struck and Aguiar's case was dismissed. In a September 2011 order, the court reinstated Aguiar's defense but not his claims against Kaplan; Aguiar's defenses were further clarified in July of 2012. An appeal is pending to reinstate Aguiar's claims against Kaplan.

Dershowitz dismisses the idea that Aguiar thought he was the Messiah. “As far as I know, he never thought he was the Messiah,” he says of Aguiar. “His uncle knew about his emotional difficulties and exploited them to the hilt and pressed every conceivable button he could in an effort to drive Guma crazy, to provoke him.”

Indeed, in a separate third-party complaint by Aguiar’s wife, Jamie, against Kaplan, filed in May 2012 in Broward County, Fla., Jamie alleged that “Kaplan, knowing the vulnerability created by Guma’s bi-polar condition, employed a team of security specialists to create a paranoid meltdown.” The complaint, which sought damages in excess of $15,000, says that “Kaplan’s campaign included the expenditure of millions of dollars by Kaplan on former Israeli Defense Force Commandos who were asked to intimidate, confuse, and disorient Aguiar and his family for the purpose of ‘breaking’ him.”

The case is still pending, and a representative for Jamie Aguiar said she wasn’t available for an interview. An attorney for Aguiar’s mother, Ellen, didn’t respond to repeated requests for comment. Kaplan’s lawyer, Tropin, declined to comment on these allegations specifically.

“I would say it like this,” said Levine, the documentarian. “Different people who have bipolar disorder have different triggers, and this was a guy who had all kinds of stress in his life. He was juggling a million things. He was constantly innovating. He was first of all a person who never slept very much, which is how he was so successful.”

When “things would start going off a little bit, be it stress from his marriage or stress from his uncle or a lawsuit,” Levine said Aguiar “would start slipping.”

According to rabbis Singer and Lipskar, there could be another, more reasonable explanation for Aguiar’s assertion that he had a “messianic” stature, one grounded in some interpretations of Jewish theology. “In a very normal way he was thinking maybe God would use him,” Singer said.

It’s the same answer Aguiar himself gave in a 2009 interview to The Jerusalem Post. In a video, he doesn’t appear unbalanced, but rather a focused young man talking in all seriousness about his beliefs—more celebrity than deluded demigod. Shown in a light purple checked shirt undone to the third button and with a small Star of David hanging from a cord around his neck, Aguiar is asked by a reporter off screen if he thinks “God sent you here, to come to Jerusalem?” Aguiar says he does, “however, he did the same thing for you … and for all of the Jews that are out there. All of us have been called to help the Jewish people, and ultimately to help the world.”

“I hope I die in Jerusalem,” Aguiar said later in the interview. “I hope that I’m here for the rest of my life.” Then he rephrases. “Actually, I don’t want to die, but I hope I’m here for the rest of my life.”

In July, two conservators were appointed to oversee Aguiar’s interests, dividing responsibility for his fortune and pending litigation.

Dershowitz says he and Aguiar had planned to go to a basketball game on the night of the disappearance, but the lawyer couldn’t make it. After hearing the news, Dershowitz said he kept hoping his friend would call him from and say he was alive and well. “I was hoping against hope maybe the phone would ring. It never did.”

This article has been emended from its original version to reflect the fact that Guma Aguiar's claims against Thomas Kaplan and his interests were struck in 2010.